title: A tandem organocatalytic α-chlorination-aldol reaction that proceeds with dynamic kinetic resolution: a powerful tool for carbohydrate synthesis.
abstract: A tandem, proline-catalyzed α-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of α-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis of carbohydrates.
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada.
authors.forename: Milan
authors.initials: M
authors.lastname: Bergeron-Brlek
authors.forename: Timothy
authors.initials: T
authors.lastname: Teoh
authors.forename: Robert
authors.initials: R
authors.lastname: Britton
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D054879:Halogenation; D007700:Kinetics; D056004:Molecular Dynamics Simulation; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D011392:Proline